New Windsor Holidays from £451

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Your New Windsor Holiday

There's no better way to travel than with one of our holiday packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. Dia Beacon, Storm King Art Centre and Ice Time Sports Complex are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor holiday on Expedia.

Top New Windsor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Manchester (MAN) to Newburgh (SWF)
5.4/10 (1,021 reviews)
Nice reasonable place to stay

Reviewed on 20 Jul 2025

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
24 Sept - 29 Sept
found 23 hours ago
Return flight included
Manchester (MAN) to Newburgh (SWF)
5.2/10 (1,000 reviews)
Toilet consistently running all night and TV remote not working

Reviewed on 21 Jul 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
24 Sept - 29 Sept
found 23 hours ago
Return flight included
Manchester (MAN) to Newburgh (SWF)
7.4/10 Good! (492 reviews)
If you like dirty over priced motels then this the place for you. Make sure your cellphone is charged because their is no phone in the room.

Reviewed on 2 Aug 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Manchester (MAN) to Newburgh (SWF)
5.8/10 (1,005 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on 8 Jul 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
16 Oct - 19 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Newburgh (SWF)
8.4/10 Very Good! (1,012 reviews)
It was clean and close to a couple restaurants. The shower was nice. It had good pressure and great hot water. For the price I thought it would include breakfast. I usually only stay at places with free breakfast, but it was late and I didn’t notice it when I booked. The bed was super hard. The room was small and smelled a little musty when we got there. Thankfully we were on the second floor and it was a nice night, so we opened the windows. All in all I would stay again if the price was a little lower.

Reviewed on 3 Aug 2025

New Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
8,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, SplashDown Beach and Dia Beacon

Top hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is £101 per night from 10 Aug to 11 Aug
£101
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Lovely 2 day stay
"The room was clean, the beds were super comfortable. Check in was easy."

Reviewed on 27 Jul 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is £151 per night from 10 Aug to 11 Aug
£151
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Clean and well-kept property. Conveniently located near Stewart Newburgh Airport. Breakfast options were a bit disappointing, but overall, a good place to stay. Safe and quiet."

Reviewed on 3 Aug 2025

Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is £96 per night from 25 Aug to 26 Aug
£96
25 Aug - 26 Aug
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"The hotel is unique and provides so many amenities! First we were greeted by very friendly and helpful staff at check in! Our room was clean and the lodge has a beautiful common area and view. The zoo, museums and park area is amazing! So many trails to take all within the park. Can’t wait to come ..."

Reviewed on 2 Aug 2025

Overlook Lodge at Bear Mountain
See all 986 properties in New Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in New Windsor

Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

£118
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

£580
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

Frequently asked questions

How much does a New Windsor travel package cost?
Go from wondering to wandering with our New Windsor travel packages, which start from just £451. Pick the hotels and flights that suit your plans. Then, add on one or two experiences or tours to round off your unique escape.
If I'm not able to travel, can I cancel my New Windsor travel package?
Don't worry if you're rethinking your New Windsor travel package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to New Windsor?
Combine your hotels and flights, throw in extras such as tours, and save with a New Windsor travel package. You won't just walk away with awesome discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later New Windsor holidays?
Expedia has partnered with online lender Klarna to make your next getaway a bit easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in New Windsor?
A holiday in New Windsor isn't complete without stopping by New York Military Academy, Mount Saint Marys College Newburgh and Washington Headquarters. Stay close to these sights and make sightseeing easy.
What are the top hotels in New Windsor?
Red Roof Inn & Suites Newburgh – Stewart Airport in the Vails Gate neighbourhood is a wonderful choice for a New Windsor holiday. Reserve a room here and you'll be well-placed to get out and explore all that this buzzing city has to offer.
How far in advance should I book my New Windsor holiday?
While not all air carriers advertise ticket prices early, you can usually look up international flights on Expedia up to 12 months in advance. This is when you can nab some incredible bargains. If you're booking last minute, there's a chance you could get lucky. Low prices occasionally emerge just weeks prior to departure.
What does an Expedia New Windsor travel package include?
With Expedia, you can choose a combination of flights, hotels and car rentals to build your perfect New Windsor travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Don't forget, the more you bundle, the more cash you'll save!
What should I know before booking a New Windsor travel package?
An Expedia travel package can be customized for your circumstances and is a simple way to make your money go further. How little or much you include is totally up to you. Rental cars, hotels and flights — mix and match whatever combination suits your style.
Can I choose my airline with a New Windsor Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Just pick the carrier that suits you and craft the perfect New Windsor escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.